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CAS No. : | 21419-48-7 | MDL No. : | MFCD02228849 |
Formula : | C8H6BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FHCKWLXHKAPOBN-UHFFFAOYSA-N |
M.W : | 224.06 | Pubchem ID : | 728935 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.4% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; | To a stirred solution of compound 9A (reference: US 2009/0163489 Al) (0.3 15 g, 1.24 mmol) and 2-chloro-3-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyridine (Reference WO 2015157093 Al/WO 2015044172 Al/WO 2014055955 Al) (0.445, 1.86 mmol) in 1,4- dioxane (9 mL) and water (3 mL) was added Na2CO3 (0.3 94 g, 3.72 mmol). The reaction mixture was degassed for 3 mm. and then to it was added Pd(PPh3)4 (0. 143g, 0.124 mmol), and the resultant mixture was heated at 100 C for 12 h. The reaction mixture was then filtered through a Celite pad, the filter cake washed with ethyl acetate and the combined filtrate evaporated under reduced pressure to give the cmde compound. It was purified via silica gel chromatography (24 g Redisep column, eluted with 60 % ethyl acetate in petroleum ether) to furnish N-(6-(2-chloropyridin-3-yl)imidazo[ 1 ,2-ajpyridin-2-yl)acetamide 9B (211 mg, 0.736 mmol, 59.4 % yield) as a light yellow solid. LCM5: m/z = 385.0 [M+Hf?; ret. time 1.49 mm; condition C. Compound 19B was synthesized by reacting 19A (reference: Angew. Chem. mt. Ed. 2014, 53, 305-309) and 2-chloro-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine employing the experimental procedure described for compound 9B as shown in Scheme 16. The crude residue was purified by silica gel chromatography (40 g RediSep column, eluting with a gradient of 35% ethyl acetate in petroleum ether) to yield 6-(2-chloropyridin-3- yl)quinazolin-4-amine 18B (0.6g, 2.337 mmol, 52.4 % yield). LCMS: m/z = 257.2 [M+Hf?; ret. time 1.06 mm; condition E. |
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